So you’re a middle-aged divorced guy. You’re on your own. Back in the game. Out on the prowl. Making the scene. What’s a man recently back on the market gotta do to get his groove on?

For one thing, stop talking like that — you sound like the wacky neighbor in a 70s sitcom. And here are four other things you really need to not be doing with yourself. We know they might be tempting, but trust me: don’t be that guy.

1. Boy Band Hair.

I know you want to look younger. Everybody does. But frosted tips are not the answer. Ditto fauxhawks or mohawks or hair extensions, unless you left your wife to join a Whitesnake tribute band. You will not look younger or cooler. You will look like a creepy douchebag, or the kind of dude who might leave long handwritten lyrics duct-taped to Justin Timberlake’s front gate in the middle of the night.

Thompson-twins-tom2“Well, here I go again on my own.” (Image: Wikipedia)

Generally, if you go to a halfway decent barber or hairstylist, they’ll be able to give you a new ‘do that’s within acceptable taste boundaries without being too boring. And if you’re thinning on top, it’s completely acceptable to shave your head these days.

Just don’t go adding any scalp tattoos to the mix. You want to look like you can handle yourself, not like you’re trying to get a job as a meth cook.

2. The Island Life


3075460257_2c6e32be13_z“Can you believe this shirt was on sale?” (Image: Kate Webster via Flickr)

You might think that a middle-aged divorced guy rocking a Hawaiian shirt and big shorts tells the world: “I’m a free spirit who’d rather be living the good life in a laid-back tropical paradise.” But what it actually says is: “I drink homemade margaritas from a Slurpee cup and cry myself to sleep listening to Jimmy Buffett in my studio apartment.” Ditto Cuban shirts, straw fedoras, white linen suits, and most importantly, socks under sandals.

(Seriously. Don’t be the sock under sandals guy. Ain’t nobody got time for that.)

3. Sweet Ride, Bro

Sure, I get it. You drive past that classic car dealership in your boxy little sedan and see that 1964 Corvette Stingray, and that “chikka chikka” song from Ferris Bueller’s Day Off starts playing in your head, and you can just imagine it: out on the open road, just you and some sorority girls, the wind in your hair….

“Does it come with a white Armani suit and a side of desperation?” (Image: Wikipedia)

Well, keep imagining, Don Draper, because the sad truth of the world is this: nobody who can afford a cherry ride like that actually looks cool in it, and nobody who looks cool in it can actually afford it. And you’d be working so much overtime to pay it off that the only open road you’d ever see is the employee parking lot.

If you really want that smooth Steve McQueen car, a better option might be to buy an old junker and learn to fix it up yourself on weekends. You’ll be picking up a new hobby and a set of skills — never a bad thing — and you’ll have the pride of knowing you didn’t just throw money at your middle-aged divorce guy crisis; you threw time and effort and a lot of aching back muscles in too.

And as for the sorority girls, well….

4. Young Girl, Get Out Of My Life

You ever see Twilight? You ever think to yourself “Dude, that vampire guy is like a hundred years old. What does he possibly have in common with some teenage girl? I mean, what? Does he hold her tenderly as they lie in bed and tell her all about that one time he saw Rita Hayworth driving down Hollywood Boulevard in her Studebaker?”

Yeah. And you don’t even look like Robert Pattinson, guy.

“Excuse me, miss, may I buy you a chocolate milk? Miss? Where are you going?” (Image: Wikipedia)

Hot young girls may seem like the answer to a myriad of life’s problems, like self-esteem, boredom, a lack of strenuous physical activity…but what they actually are is a psychosexual circus in which you play a starring role as the World’s Most Delusional Man.

Manage Your Middle-aged Divorced Guy Expectations

Okay, maybe that’s a bit harsh — sometimes spring/autumn romances do work out. But what do you really have in common with that twenty year old barista at Starbucks, other than a mutual appreciation for chai lattes and the way her butt looks in khaki slacks? Real relationships are based upon shared experience and goals; you need to find someone who’s a match for your life experience and maturity, someone who can be an equal partner as you move ahead from your middle-aged divorced guy starting point.

And before you start whining that women your own age just don’t do it for you, remember this: Rene Russo is sixty years old. If you’d really trade in a beautiful, intelligent woman like that for some perky blonde barely out of her teens, well…you’ve got worse problems than a mid-life crisis, son.


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(c) Can Stock Photo / lisafx

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